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$413+ Cheap flights from Aspen (ASE) to Midway (MDW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Aspen to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Aspen (ASE) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 14, 2025.

Round-trip from

$413
(Delta)

Popular in

March

Cheapest in

April

Average price

$340
From Aspen Pitkin County to Chicago Midway
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($41 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Aspen to Midway

Cheapest flights from Aspen to Midway
Explore the most affordable flight options available from Aspen to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/57:16 amASE - MDW
2 stops10h 21mDelta
Mon 9/86:00 amMDW - ASE
1 stop6h 21mDelta
Deal found 8/14$413
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/47:16 amASE - MDW
2 stops10h 21mDelta
Sun 9/76:00 amMDW - ASE
1 stop6h 21mDelta
Deal found 8/14$469
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/67:16 amASE - MDW
2 stops10h 21mDelta
Tue 9/96:00 amMDW - ASE
1 stop6h 21mDelta
Deal found 8/14$669
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/117:16 amASE - MDW
2 stops10h 19mDelta
Sun 9/146:00 amMDW - ASE
1 stop6h 13mDelta
Deal found 8/14$874
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/297:16 amASE - MDW
2 stops10h 21mDelta
Tue 9/26:00 amMDW - ASE
1 stop6h 21mDelta
Deal found 8/14$894
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/307:16 amASE - MDW
2 stops10h 19mDelta
Thu 10/96:00 amMDW - ASE
1 stop6h 10mDelta
Deal found 8/14$914
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/127:16 amASE - MDW
2 stops10h 19mDelta
Sun 9/146:00 amMDW - ASE
1 stop6h 13mDelta
Deal found 8/14$1,074
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:16 amASE - MDW
2 stops10h 19mDelta
Fri 10/106:00 amMDW - ASE
1 stop6h 10mDelta
Deal found 8/14$1,244

Cheapflights Fare Finder

 
Customize your flight search to find flights from Aspen to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
Use the filters below to find and compare flights from Aspen to Chicago Midway Airport that are best for you.

Fly from

Aspen

Fly to

Midway

Route

Depart

Return

Price

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Fri 9/5

7:16 am-6:37 pm

2 stops10h 21m

Chicago Midway

Mon 9/8

6:00 am-11:21 am

1 stop6h 21m

$413

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Thu 9/4

7:16 am-6:37 pm

2 stops10h 21m

Chicago Midway

Sun 9/7

6:00 am-11:21 am

1 stop6h 21m

$469

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Sat 9/6

7:16 am-6:37 pm

2 stops10h 21m

Chicago Midway

Tue 9/9

6:00 am-11:21 am

1 stop6h 21m

$669

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Thu 9/11

7:16 am-6:35 pm

2 stops10h 19m

Chicago Midway

Sun 9/14

6:00 am-11:13 am

1 stop6h 13m

$874

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Fri 8/29

7:16 am-6:37 pm

2 stops10h 21m

Chicago Midway

Tue 9/2

6:00 am-11:21 am

1 stop6h 21m

$894

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Tue 9/30

7:16 am-6:35 pm

2 stops10h 19m

Chicago Midway

Thu 10/9

6:00 am-11:10 am

1 stop6h 10m

$914

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Fri 9/12

7:16 am-6:35 pm

2 stops10h 19m

Chicago Midway

Sun 9/14

6:00 am-11:13 am

1 stop6h 13m

$1,074

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Mon 9/29

7:16 am-6:35 pm

2 stops10h 19m

Chicago Midway

Wed 10/8

6:00 am-11:10 am

1 stop6h 10m

$1,074

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Tue 9/2

7:16 am-6:37 pm

2 stops10h 21m

$1,206

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Sun 9/28

7:16 am-6:35 pm

2 stops10h 19m

$1,206

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Best time to book a flight from Aspen to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Aspen with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Aspen to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Aspen to Chicago Midway?

    Located just 3.5 mi from the city center, Aspen Pitkin County is the airport most travelers will use when flying to Chicago Midway from Aspen. Booking flights from Pitkin County (ASE) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 0 different airlines.

  • Can I find deals for flights from Aspen to Midway that include hotel bookings?

    Yes. In addition to deals on Aspen to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Aspen to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Aspen to Midway.

  • Can I find deals for business class flights from Aspen to Midway?

    Yes. Cheapflights offers flight deals from Aspen to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Aspen to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Aspen to Chicago Midway Airport (average of $160). Flying from Aspen to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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